Brad Pitt had no idea he and Ellen DeGeneres shared a connection—until she threw him a curveball about dating one of his ex-girlfriends

It seems like Brad Pitt has no idea about Ellen DeGeneres’ dating history! While making an appearance on ‘The Ellen DeGeneres Show’ in 2019, the Emmy-winning actor learned that he and the late-night talk show host have something in common: An ex-girlfriend! Talk about awkwardness. During their conversation, Pitt recalled knowing DeGeneres since the “late ’80s, early ’90s.” When she asked if he remembered their first encounter, Pitt had a vague memory but was certain they met at Melissa Etheridge’s pool party.

While recalling their initial encounter, Pitt said, “I remember a Melissa Etheridge pool party, where I think you were hitting on my girlfriend.” DeGeneres immediately quipped, “Was I hitting on your girlfriend, really?” To which Pitt said, “I think so. I was flattered.” After reminiscing for a moment, DeGeneres casually revealed that she had once dated one of Pitt’s ex-girlfriends. “I actually, since then, have dated another one of your girlfriends. We’ll talk about that later,” she said. DeGeneres, who didn’t disclose the ex-girlfriend added, “We’ll talk about that later.” Pitt playfully said, “After the show.”

To this day, neither Pitt nor DeGeneres has revealed the identity of the ex-girlfriend in question. As for DeGeneres, she has been happily married to Portia de Rossi since 2008. The couple first met at a Rock the Vote concert in 2001 and hit it off instantly. In an interview with People magazine, de Rossi shared that it was love at first sight for her. “I remember thinking that she was the coolest, most fascinating, beautiful, funniest person I’d ever met,” de Rossi told the media outlet.

However, DeGeneres and Rossi didn’t start dating until 2004. At the time, DeGeneres was with photographer Alexandra Hedison, while, de Rossi was in a relationship with singer Francesca Gregorini. After ending their respective relationships, they began dating and made their first public appearance as a couple at a Golden Globe Awards afterparty in January 2005. Nearly four years later, they announced their engagement in May 2008 and tied the knot that August after gay marriage was legalized in California. In February 2023, the duo renewed their vows at de Rossi’s birthday party and they are still going strong.

On the other hand, Pitt has been married twice before. He first tied the knot with ‘Friends’ actress Jennifer Aniston in 2000, but their marriage ended in 2005, with the divorce finalized in October of that year. Following his split from Aniston, Pitt began dating his ‘Mr. & Mrs. Smith’ co-star Angelina Jolie and the two got hitched in 2014. However, their relationship soured, and Jolie filed for divorce in 2016, citing “irreconcilable differences.” Following a lengthy legal battle, they finalized their divorce in 2024. The former couple shares six children: Maddox, Pax, Zahara, Shiloh, and twins Vivienne and Knox. Currently, Pitt is rumored to be dating Ines de Ramon, though neither has confirmed the speculation, as per ELLE.